The Stockton family is uber wealthy and theirs is Old Money. Their private school auctions off eight-thousand-dollar teddy bears; yacht and golf club memberships are a given; and their homes are protected by the New York City historical preservation society. Marrying outside of their class is quietly frowned upon (for fear of diluting their wealth) and prenups are a given for the three adult Stockton siblings.
Sasha marries into the Stockton family and is referred to as the Gold Digger behind her back by her husband Cord's two sisters, Georgiana and Darley. When Tilda and Chip Stockton, Cord's parents, move into a nearby luxury condo, Cord and Sasha are pressured to move into the family home on Pineapple Street in Brooklyn Heights. The house is huge and brimming with family heirlooms and detritus, of which Sasha's mother-in-law will not let her dispose. Sasha does not want to live there, and she feels like an intruder from Cord's family's chilly behavior towards her.
Darley forfeits her trust fund when she marries Malcolm because she refuses to ask him to sign a prenup. This comes back to haunt her, along with her decision to give up her successful career to stay home with their kids, after Malcolm loses his lucrative job in finance.
Georgina works at a non-profit and enjoys the thought of doing good work in the world. Nevertheless, she takes advantage of the benefits of her family's money as she can live wherever she wants and buy clothes and other things without a thought. When Georgiana's love interest with a work colleague goes terribly wrong it triggers an existential crisis. She begins to question her morality and how growing up in the top one percent has affected her.
Jenny Jackson's character development is outstanding, and her descriptions of scenes had me in stitches! When the Stocktons ask Sasha what it was like "growing up poor" (their words), they listen to her detailing her ordinary, middle-class childhood "as though she were describing an upbringing in a yurt on the salt flats". And as Georgiana is confiding in her mom about feeling like she's doing nothing to make the world a better place, her mom replies that when SHE feels like that, she buys herself flowers.
This novel had me slowing down at the end because I didn't want it to end. Comedic and entertaining, Pineapple Street is a family drama and a thoughtful commentary on classism. Mostly, it's a hugely enjoyable, funny read! I give Jenny Jackson's first book an enthusiastic five out of five stars.
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